Water → N-[2-(4-amino-7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide

HRID 2383118Notes

Reaction equation

HRID 2383118 reaction equation
[OH-].[NH4+:2].[CH2:3]([O:10][C:11]1[CH:12]=[CH:13][C:14]2[C:15]3[N:24]([CH2:25][C:26]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])([CH3:28])[CH3:27])[C:23]([CH2:34][O:35][CH2:36][CH3:37])=[N:22][C:16]=3[CH:17]=[N+:18]([O-])[C:19]=2[CH:20]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.O>ClCCl.C(Cl)(Cl)Cl.CO>[NH2:2][C:17]1[C:16]2[N:22]=[C:23]([CH2:34][O:35][CH2:36][CH3:37])[N:24]([CH2:25][C:26]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])([CH3:28])[CH3:27])[C:15]=2[C:14]2[CH:13]=[CH:12][C:11]([O:10][CH2:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)=[CH:20][C:19]=2[N:18]=1

Participants

8

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 67051025N-[2-(7-benzyloxy-2-ethoxymethyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide

Product 1

HCID 57545342N-[2-(4-amino-7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Concentrated ammonium hydroxide (3 to 4 mL) was added to a solution of N-[2-(7-benzyloxy-2-ethoxymethyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide (1.75 g, 3.51 mmol) in dichloromethane (35 mL) with rapid stirring. p-Toluenesulfonyl chloride (670 mg, 3.51 mmol) was added. The reaction was stirred for one hour; a precipitate formed. Water (100 mL) was added, and the dichloromethane was removed under reduced pressure. Dichloromethane (5 mL) was then added with rapid stirring, and the resulting powder was isolated by filtration and dissolved in 90:10 chloroform:methanol (200 mL). The resulting solution was concentrated under reduced pressure, and the residue was triturated with hot propyl acetate (50 mL), isolated by filtration, and dried under reduced pressure to provide 1.45 g of N-[2-(4-amino-7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide as a tan powder.

Workup

  1. customa precipitate formed
  2. customthe dichloromethane was removed under reduced pressure
  3. additionDichloromethane (5 mL) was then added with rapid stirring
  4. customthe resulting powder was isolated by filtration
  5. concentrationThe resulting solution was concentrated under reduced pressure
  6. customthe residue was triturated with hot propyl acetate (50 mL)
  7. customisolated by filtration
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-525ffa4830b845c297c0f66330610603
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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